Question
The diethyl ester of this compound forms part of the catalyst in the Sharpless epoxidation, with the chirality of this compound determining the chirality of the product. For 10 points each:
[10e] Name this four-carbon dicarboxylic acid with two chiral centers whose salts crystalize from wine. The facts that it rotates light and that its salts form asymmetric crystals of only one enantiomer were key to Pasteur’s study of chirality.
ANSWER: tartaric acid [or tartrate; or bitartrate; or 2,3-dihydroxysuccinic acid; or 2,3-dihydroxysuccinate; or 2,3-dihydroxybutanedioic acid; or 2,3-dihydroxybutanedioate]
[10h] This axially chiral compound was used as a chiral auxiliary in the synthesis of limonene. Many of its derivatives are also chiral auxiliaries or catalysts, including Shibasaki catalysts and ALB, as well as BINAP.
ANSWER: BINOL [or 1,1’-bi-2-naphthol; or 1,1’-binaphthol; or [1,1’-binaphthalene]-2,2’-diol]
[10m] Synthesis of the Wieland–Miescher ketone uses this chiral organocatalyst that makes the aldol reaction asymmetric. The study of asymmetric organocatalysis began with this amino acid, whose catalytic activity is due to its secondary amine.
ANSWER: proline [or Pro; or P; or pyrrolidine-2-carboxylic acid]
<Gerhardt Hinkle, Chemistry>
Summary
| 2023 Penn Bowl @ Waterloo | 10/28/2023 | Y | 4 | 10.00 | 50% | 50% | 0% |
| 2023 Penn Bowl @ FSU | 10/28/2023 | Y | 1 | 10.00 | 100% | 0% | 0% |
| 2023 Penn Bowl (Harvard) | 10/21/2023 | Y | 3 | 10.00 | 67% | 33% | 0% |
| 2023 Penn Bowl (Mainsite) | 10/21/2023 | Y | 7 | 4.29 | 29% | 14% | 0% |
| 2023 Penn Bowl (Norcal) | 10/28/2023 | Y | 2 | 5.00 | 0% | 50% | 0% |
| 2023 Penn Bowl (South Central) | 10/28/2023 | Y | 3 | 0.00 | 0% | 0% | 0% |
| 2023 Penn Bowl (UK) | 10/28/2023 | Y | 5 | 16.00 | 80% | 60% | 20% |
| 2023 Penn Bowl @ UNC | 10/28/2023 | Y | 2 | 20.00 | 50% | 100% | 50% |